A prodrug form of itaconate
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4-octyl Itaconate

Item No. 25374

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methylene-butanedioic acid, 4-octyl ester
CAS Number
3133-16-2
Molecular Formula
C13H22O4
Formula Weight
242.3
Purity
≥98% (mixture of tautomers)
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
SMILES
O=C(CC(C(O)=O)=C)OCCCCCCCC
InChi Code
InChI=1S/C13H22O4/c1-3-4-5-6-7-8-9-17-12(14)10-11(2)13(15)16/h2-10H2,1H3,(H,15,16)
InChi Key
KBASUIDPDITQHT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

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    50 mg

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    100 mg

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    250 mg

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    Cayman Chemical
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    Product Description

    4-octyl Itaconate is a prodrug form of itaconate, an endogenous cellular metabolite produced via decarboxylation of cis-aconitate by the enzyme encoded by IRG1.1,2 It is hydrolyzed to itaconate by esterases in C2C12 cells and LPS-activated mouse macrophages where it acts as a regulator of macrophage function with anti-inflammatory properties.2 4-octyl Itaconate increases nuclear factor erythroid 2-related factor 2 (Nrf2) protein levels and expression of Nrf2 target genes and enhances LPS-induced Nrf2 stabilization in mouse macrophages. In vivo, 4-octyl itaconate (50 mg/kg) decreases serum levels of IL-1β and TNF-α, increases Nrf2 protein expression, and protects against LPS-induced lethality in wild-type, but not Nrf2 knockout, mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Michelucci, A., Cordes, T., Ghelfi, J., et al. Immune-responsive gene 1 protein links metabolism to immunity by catalyzing itaconic acid production. Proc. Natl. Acad. Sci. USA 110(19), 7820-7825 (2013).

    2. Mills, E.L., Ryan, D.G., Prag, H.A., et al. Itaconate is an anti-inflammatory metabolite that activates Nrf2 via alkylation of KEAP1. Nature 556(7699), 113-117 (2018).